4-substituted phenyl pyridazine compound and herbicidal activity

A compound and substituent technology, applied in the field of 4-substituted phenylpyridazine compounds and herbicidal activity

Inactive Publication Date: 2005-10-05
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Most of the pyridazine herbicides reported in the literature are compounds with phenyl substitutions at the 2-

Method used

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  • 4-substituted phenyl pyridazine compound and herbicidal activity
  • 4-substituted phenyl pyridazine compound and herbicidal activity
  • 4-substituted phenyl pyridazine compound and herbicidal activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1: 4,5-dihydro-6-methyl-3-pyridazinone

[0036] 42.3 g of ethyl levulinate and 27.9 g of hydrazine hydrate were mixed, and a small amount of ethanol was added to obtain a homogeneous solution. The mixture was heated to boiling, refluxed for 1 hour, cooled to room temperature, and left overnight to obtain colorless flaky crystals of 4,5-dihydro-6-methyl-3-pyridazinone with a yield of 96%.

Embodiment 2

[0037] Example 2: 6-methyl-3-pyridazinone

[0038] Dissolve 55g of 4,5-dihydro-6-methyl-3-pyridazinone in 120ml of freshly steamed glacial acetic acid, slowly drop in 33ml of liquid bromine, heat to reflux after dripping, and place it overnight after reflux for 15min. The reaction solution was suction filtered to obtain a complex of 6-methyl-3-pyridazinone and hydrogen bromide. Dissolve 22.4 g of the obtained complex of 6-methyl-3-pyridazinone and hydrogen bromide in 85 ml of glacial acetic acid, add 13.5 g of anhydrous sodium acetate, heat the mixture to boiling, and reflux for 1 h. The solvent was distilled off under reduced pressure, and the residue was added to ice water to obtain a white solid, which was filtered with suction and dried to obtain 12.9 g of a white solid with a yield of 80%.

Embodiment 3

[0039] Example 3: 4-(3-trifluoromethylphenyl)-6-methyl-3-pyridazinone

[0040] 10 mmol of 6-methyl-3-pyridazinone was dissolved in 50 ml of anhydrous tetrahydrofuran, and 40 mmol of 3-trifluoromethylphenylmagnesium bromide in tetrahydrofuran was added at room temperature. The mixture was heated to boiling, refluxed for 5 hours and then hydrolyzed with saturated ammonium chloride solution. The organic phase was washed with saturated sodium chloride solution, dried, spin-dried and separated by column chromatography. The eluent was ethyl acetate:petroleum ether , to give 4-(3-trifluoromethylphenyl)-6-methyl-3-pyridazinone and 4,5-dihydro-4-(3-trifluoromethylphenyl)-6-methyl -3-pyridazinone, the yields were 38.58% and 16.89%, respectively.

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Abstract

This invention relates to 4-substitued phenyl pyridazine chemical compound and its weed killing reactivity. The chemical compounds (I)(II) have high weed killing reactivity. It can effectively kill the one-year ruderal and broad-leave weed. There after, R1: H, alkyl, alkoxyl, alkylogen, alkylogen oxide, halogen and etc; R2, H, alkyl, alkoxyl, phenyl alkoxyl, hydroxyl phenyl, alkoxyl alkyl, alkylogen, alkylogen alkoxyl, nitryl, cyan, alkyl amine, dialkyl, acetylamino and etc; R3:H, phenyl, hydroxyl phenyl, alkoxyl, alkylogen, halide, alkyl halide and etc; R4: H, benzoxazole, substituted benzoxazole base, benzothiazole and etc; R5: H, alkyl, alkylogen: R6R7: H, alkyl, R6, R7 can be the same or different, n=1 or 2.

Description

technical field [0001] The present invention relates to 4-substituted phenylpyridazine compounds and their herbicidal activity. Background technique [0002] Herbicides and phytohormones affect or block normal plant metabolism, including photosynthesis, formation of sugars, lipids or amino acids, and biosynthesis of specific cellular components. Albino herbicides can inhibit the synthesis of carotenoids, and their toxic effects on plants are related to the functions of carotenoids. [0003] Carotenoids in chloroplasts have a dual role, on the one hand as a light absorber in photosynthesis; on the other hand as a protective substance in photosynthesis. They acquire several active states during the process of exciting chlorophyll by light. The action of triplet chlorophyll and oxygen molecules converts energy into singlet oxygen. Singlet oxygen is highly reactive and can oxidize any molecule in its vicinity. Carotenoids protect chloroplasts, but they cannot do so when the ...

Claims

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Application Information

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IPC IPC(8): A01N43/58C07D237/14
Inventor 杨华铮许寒邹小毛胡方中刘斌杨秀凤
Owner NANKAI UNIV
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